4-[1-(4-methoxy-phenyl)-propenyl]-morpholine | 55482-46-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-[1-(4-methoxy-phenyl)-propenyl]-morpholine
• 英文别名: p-methoxypropiophenone morpholine enamine
• CAS: 55482-46-7；64274-08-4
• 化学式: C₁₄H₁₉NO₂
• 分子量: 233.31
• InChiKey: JSYFHXZCRGJDED-BNNQUZSASA-N

物化性质

• 沸点：
  390.9±41.0 °C(Predicted)
• 密度：
  1.065±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.39
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  21.7
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-[1-(4-methoxy-phenyl)-propenyl]-morpholine 在 甲醇 、 9-borabicyclo[3.3.1]nonane dimer 、 sodium azide 、 间氯过氧苯甲酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 63.17h， 生成 threo-1-azido-2-hydroxy-1-(4-methoxyphenyl)propane
  参考文献：
  名称：

  Acid-catalyzed hydrolysis of cis- and trans-anethole oxides: discrete carbocation intermediates and syn/anti hydration ratios

  摘要：

  Rate and product studies of the hydronium ion-catalyzed hydrolysis reactions of trans-anethole oxide (12b) and its geometric isomer, cis-anethole oxide (13b), were carried out. Acid-catalyzed hydrolysis of trans-anethole oxide is 50 times faster than that of its cis isomer and this difference in reactivity is attributed to steric interactions between the cis-beta-CH3 and the aryl group in the transition state for hydrolysis of cis-anethole oxide that are not present in the transition state for the acid-catalyzed hydrolysis of trans-anethole oxide. Carbocation intermediates in the hydrolysis of both 12b and 13b are trapped, subsequent to their rate-limiting formation, by azide ion. Identical diol product mixtures from the acid-catalyzed hydrolysis of both 12b and 13b, and identical azide product mixtures from their reactions in solutions at low pH containing sodium azide, suggest that both 12b and 13b react to form a common discrete carbocation intermediate and that products are derived from reaction of this intermediate with nucleophiles. Molecular modeling calculations suggest that there are three minimum energy conformations of this carbocation intermediate. Results are interpreted in terms of a mechanism in which rotation about the C(alpha)-C(beta) bond of the intermediate is rapid relative to the rate at which it reacts with solvent or other nucleophiles. Mechanisms involving concerted addition of solvent are ruled out.

  DOI：

  10.1021/jo00062a006
• 作为产物：
  描述：

  吗啉 、 对甲氧基苯丙酮 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 240.0h， 生成 4-[1-(4-methoxy-phenyl)-propenyl]-morpholine
  参考文献：
  名称：

  Acid-catalyzed hydrolysis of cis- and trans-anethole oxides: discrete carbocation intermediates and syn/anti hydration ratios

  摘要：

  Rate and product studies of the hydronium ion-catalyzed hydrolysis reactions of trans-anethole oxide (12b) and its geometric isomer, cis-anethole oxide (13b), were carried out. Acid-catalyzed hydrolysis of trans-anethole oxide is 50 times faster than that of its cis isomer and this difference in reactivity is attributed to steric interactions between the cis-beta-CH3 and the aryl group in the transition state for hydrolysis of cis-anethole oxide that are not present in the transition state for the acid-catalyzed hydrolysis of trans-anethole oxide. Carbocation intermediates in the hydrolysis of both 12b and 13b are trapped, subsequent to their rate-limiting formation, by azide ion. Identical diol product mixtures from the acid-catalyzed hydrolysis of both 12b and 13b, and identical azide product mixtures from their reactions in solutions at low pH containing sodium azide, suggest that both 12b and 13b react to form a common discrete carbocation intermediate and that products are derived from reaction of this intermediate with nucleophiles. Molecular modeling calculations suggest that there are three minimum energy conformations of this carbocation intermediate. Results are interpreted in terms of a mechanism in which rotation about the C(alpha)-C(beta) bond of the intermediate is rapid relative to the rate at which it reacts with solvent or other nucleophiles. Mechanisms involving concerted addition of solvent are ruled out.

  DOI：

  10.1021/jo00062a006

文献信息

• v-Triazolines—VI
  作者：Piero Dalla Croce、Riccardo Stradi

  DOI：10.1016/0040-4020(77)80036-7

  日期：1977.1